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Homeowners often hear that a roof should last 20 or 30 years. In reality, roof lifespan depends far more on local conditions  than on age alone. In areas like Winchester, roofs are exposed to seasonal temperature swings, wind-driven rain, humidity, and heavy tree coverage. These factors can significantly accelerate wear — especially when ventilation or flashing is inadequate. Two roofs installed at the same time can age very differently based on: Sun exposure and shade Attic